Total synthesis of (+)-fumitremorgin B, its epimeric isomers, and demethoxy derivatives

Kodato, Shinichi; Nakagawa, Masako; Hongu, Mitsuya; Kawate, Tomohiko; Hino, Tohru

doi:10.1016/s0040-4020(01)85828-2

Cited by 63 publications

(23 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The NMR spectra were identical to the reported data. [30] BCRP inhibitory assay: The BCRP inhibitory activities of fumitremorgins 1-8 were assessed by growth inhibition of K562 cells that 926 www.chembiochem.org overexpressed the BCRP gene (K562/BCRP) by the anticancer drug SN-38, as described previously. [31] Briefly, K562/BCRP cells were grown in RPMI 1640 medium that was supplemented with fetal bovine serum (7 %, v/v) at 378C in CO 2 (5 %, v/v).…”

Section: Preparation Of Fumitremorginsmentioning

confidence: 99%

Identification of Cytochrome P450s Required for Fumitremorgin Biosynthesis in Aspergillus fumigatus

et al. 2009

View full text Add to dashboard Cite

Fumitremorgin C, a diketopiperazine mycotoxin produced by Aspergillus fumigatus, is a potent and specific inhibitor of breast cancer resistance protein (BCRP). Elucidation of the fumitremorgin C biosynthetic pathway provides a strategy for new drug design. A structure-activity relationship study based on metabolites related to the ftm gene cluster revealed that the process most crucial for inhibitory activity against BCRP was cyclization to form fumitremorgin C. To determine the gene involved in the cyclization reaction, targeted gene inactivation was performed with candidate genes in the ftm cluster. Analysis of the gene disruptants allowed us to identify ftmE, one of the cytochrome P450 genes in the cluster, as the gene responsible for the key step in fumitremorgin biosynthesis. Additionally, we demonstrated that the other two cytochrome P450 genes, ftmC and ftmG, were involved in hydroxylation of the indole ring and successive hydroxylation of fumitremorgin C, respectively.

show abstract

Section: Preparation Of Fumitremorginsmentioning

confidence: 99%

Identification of Cytochrome P450s Required for Fumitremorgin Biosynthesis in Aspergillus fumigatus

et al. 2009

View full text Add to dashboard Cite

show abstract

“…By use of methods analogous to those adopted in the synthesis21 of neosurugatoxin the pentacyclic oxindole acid (53)21 has recently been converted into prosurugatoxin (54). 50 Since the autoxidation of prosurugatoxin in the presence of 1 8 0 2 results in the formation of surugatoxin (55) enriched with l 8 0 at positions 4 and 6 it is proposed that the conversion proceeds by formation of an intermediate oxetan (56)…”

Section: Non-isoprenoid Tryptaminesmentioning

confidence: 99%

Recent progress in the chemistry of indole alkaloids and mould metabolites

Saxton¹

1989

Nat. Prod. Rep.

View full text Add to dashboard Cite

“…Verruculogen TR‐2A and fumitremorgin C, for example, are selective inhibitors of the breast cancer resistance protein (BCRP/ABCG2) . In addition, fumitremorgin C can also induce sustained tremors in animals . We have found that they have a tetrahydro‐ β ‐carboline diketopiperazines skeleton by comparing the structures, as shown in Fig.…”

Section: Introductionmentioning

confidence: 98%

“…3,8,9 In addition, fumitremorgin C can also induce sustained tremors in animals. [10][11][12][13][14][15][16] We have found that they have a tetrahydro-b-carboline diketopiperazines skeleton by comparing the structures, as shown in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis and Antimicrobial Activities of Tetrahydro‐Β‐Carboline Diketopiperazines

Zhang

et al. 2013

Chirality

View full text Add to dashboard Cite

A series of single isomers tetrahydro-β-carboline diketopiperazines were stereoselectively synthesized starting from l-tryptophan methyl ester hydrochloride and six aldehydes through a four-step reaction including Pictet-Spengler reaction, crystallization-induced asymmetric transformations (CIAT), Schotten-Baumann reaction, and intramolecular ester amidation. The chemical structures were characterized by nuclear magnetic resonance (NMR) and elemental analysis, among which two compounds were determined by x-ray single crystal diffraction. Moreover, antimicrobial activities of all the compounds were also tested.

show abstract

Total synthesis of (+)-fumitremorgin B, its epimeric isomers, and demethoxy derivatives

Cited by 63 publications

References 38 publications

Identification of Cytochrome P450s Required for Fumitremorgin Biosynthesis in Aspergillus fumigatus

Identification of Cytochrome P450s Required for Fumitremorgin Biosynthesis in Aspergillus fumigatus

Recent progress in the chemistry of indole alkaloids and mould metabolites

Enantioselective Synthesis and Antimicrobial Activities of Tetrahydro‐Β‐Carboline Diketopiperazines

Contact Info

Product

Resources

About